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Copper/H2O2-mediated oxidation of 2'-deoxyguanosine in the presence of 2-naphthol leads to the formation of two distinct isomeric adducts.

The Journal of organic chemistry (2011-08-27)
Aaron M Fleming, Arunkumar Kannan, James G Muller, Yi Liao, Cynthia J Burrows
ABSTRACT

Exposure of cells to phenolic compounds through exogenous and endogenous sources can lead to deleterious effects via nucleobase modifications of DNA occurring under oxidative conditions. 2'-Deoxyguanosine (dG) is the most electron rich of the four canonical bases and includes many nucleophilic sites; it is also susceptible to oxidation with numerous reactive oxygen species. In these studies, dG was allowed to react with 2-naphthol in the presence of copper or iron salts yielding two principal isomeric products. Spectroscopic analysis and reactions with alkylated nucleosides support the assignment of compound 1a/1b as a pair of atropisomer N(2) adducts and compound 2a/2b as a diastereomeric mixture of tricyclic [4.3.3.0] adducts. Both products are the result of an overall four-electron oxidation process and consequently have the same masses, though drastically different structures, providing mechanistic insight into their formation. Thus, dG alkylation by 2-naphthol under oxidative conditions yields products whose structural properties are altered, leading to potentially mutagenic effects in genomic DNA.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2-Naphthol, 99%
Sigma-Aldrich
2′-Deoxyguanosine monohydrate, 99-100%
Sigma-Aldrich
2-Naphthol, 98%
Sigma-Aldrich
2-Naphthol, fluorescence indicator, ≥99.0%
Sigma-Aldrich
2-Naphthol, BioXtra, ≥99.0% (GC)